


Wherein Dean Wears A Tutu

by Ottertotters



Category: Supernatural
Genre: Anal Fingering, Anal Play, Ballet, Blow Job, Dom/sub Undertones, Hand Jobs, Light Dom/sub, Oral Sex, Other, Sub Dean, Sub!Dean, cross dressing, dean in a tutu
Language: English
Status: Completed
Published: 2014-08-10
Updated: 2014-08-10
Packaged: 2018-02-12 15:08:36
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,439
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2114523
Author URL: https://archiveofourown.org/users/Ottertotters/pseuds/Ottertotters
Summary: <blockquote class="userstuff">
              <p>When Dean shares one of his unspoken fantasies with his current lover, he's awarded a surprise.</p>
            </blockquote>





	Wherein Dean Wears A Tutu

**Author's Note:**

> This is written from the POV of Dean's partner, whose gender and identity are completely unspecified.  
> If you're here for the smut just skip to the first line text break.  
> Also, this is the first "smutty" type thing I've ever written and I'm kind of cringing at it, but I hope you enjoy it.

“A secret?” Dean's eyebrows shot up as his green eyes widened in surprise. “Sweetheart, I've been telling you all my secrets and stories for the last year. I told you about hell, purgatory, heaven, the beatings I got from my dad, my mum dying. You know about every sexual encounter that I can remember.”

I chuckled. “I don't mean like that. I mean like... Ok. What's something you've always wanted but you're too embarrassed? Tell me a secret desire.”

“Me? Embarrassed? Hah, you know I'm not the bashful type.” Out poured the smolder and the cocky voice thick with confidence.

“You seemed pretty goddamn bashful when you told me about Rhonda Hurley's panties.” I deadpanned.

The smolder vanished “Hey! No! You promised not to use that against me!”

“I'm not! I just mean. Oh come on, we never really talked about any weird kinks you have.” The pompous eyes softened into a worried expression. “There is something! Come on, tell me.”

“Alright!” Dean shook his head. “Alright. But only if you swear not to tell Cas or Sam. Ever! Even after we're all Dead. If I die and you speak of this, I swear to God I will haunt your ass. This never leaves this room.” He gesticulated dramatically to emphasize “this room.”

I raised my palms in a gesture of surrender. “I swear.”

“Ok.” A nervous sigh left his lungs as he stared at the ceiling. “Ok, don't rush me.”

“I have all the time in the world, love.” The corners of his eyes crinkled just a little bit at “love.” “Couple years back Sam and I were working this cursed objects case. This old lady had a big ole' antiques collection. When she died her kid sold them all. And of course, it was a bunch of fucked up shit. They were all kind of unique and would like, draw victims to them.” Here he paused. Having promised to be patient, I waited. “One was a pair of ballet slippers. A dancer literally danced her legs off.” I pulled a “eegh” face. “Yeah. So we go down to the police station to recover them only to find a little girl dancing her ass off in the bathroom. Don't worry, she was fine, Sammy held her down and I yanked them off. But after that. God, it was weird. It was like they were following me and they just looked like the most beautiful things I had ever seen. All I wanted all day was to put them on. They even grew to my size.”

“Wait, hang on, this doesn't count. You spent a day being seduced by a cursed object.” I frowned.

He pulled a sass face “Well if you'd let me finish. God, I'm not done yet.”

“Sorry,” I mumbled.

“See. It wasn't just for that day. I mean it was like this crazy, needy, hungry desire for that one day. But I've kind of always wanted to be a dancer. I mean, Sammy thinks it was just for that day, because I touched them and he didn't. But I think they could feel it in me already and just fed on it.”

I waited to make sure he was finished. When he looked at me and sucked his lip I said “So your thing is you want to dance or wear ballet slippers?”

To be perfectly honest I was kind of disappointed. Our relationship up to this point had been a lot more personal and emotional. We spent far more nights up talking than fucking. I mean, don't get me wrong, we did a lot of fucking. We just never really explored that avenue very extensively. It wasn't what he needed. He needed to be held and assured and fucked gently, with lots of eye contact. Very vanilla. Dean had never had the opportunity to speak freely and explore all the shit in his head. I spent the last year coaxing it out and providing him with a safe place for that. You don't literally go to hell and back and bottle that shit up. But, of course, that's exactly what Dean Winchester did. But after a year of opening doors in his brain I was kind of hoping to open up some different, more “bedroomy” doors, to see where that could go.

“Well. I think it's a bit late for me to learn to dance. And I mean,” he scoffed humorously “I am ridiculously bowlegged, I don't think that would work out well for me. But dancers are so beautiful and graceful. And there's something about the whole ballet ensemble, the spandex and the silky slippers and the poofy skirt thing.” A vague sort of smile had spread across his face. God, he's so beautiful.

“You mean the tutu?” I hadn't meant to smirk.

“Shudup. I just. I'm so hard all the time-oh grow up that's not what I mean!” He pursed his lips at me in amused disapproval as I suppressed my sputtering giggle. “I've always had to be strong and cold for Sammy and my dad and myself. Just to survive.” The cloud that passes over his eyes when he talks about his dad always breaks my heart. “I've never been allowed to be vulnerable. I've only ever been able to even TALK like a normal human being with you. Beyond that, though. I've never been soft or gentle or... pretty. Just once. I'd like to be pretty.” I watched with rapt attention as his cheeks and ears turned pink, his eyes fixed on the ceiling. He shot me a self conscious sideways glance. I waited.

“When I was, I don't know, probably 15 or 16, we were in one of those crappy motels, but this one actually had cable. Dad was on a job and Sammy was in school, so I thought I could find porn on the tv.” He scoffs “I had no idea how to find porn except dirty magazines I'd steal at gas stations. So I found Dirty Dancing, which kind of sounds like a porno.” I nodded in agreement. “By the time I realized this was an actual movie movie, I was super into it. Watching the way they moved, like they were water. When I move, when I fight, it's like swinging a hammer. I destroy things. Evil sons of bitches, yeah. But I've never been anything other than a weapon. But watching her, watching them float around on the floor, the spins and the twirls and the lift at the end. They move with each other and pull and hold and guide each other. God, that's something so far out of my grasp I don't even know what the hell that is. But I want a piece. Just once I want to not be a weapon. Just once I want to be beautiful.”

In the year that Dean and I had spent together, he had never opened up to me like this. I mean, yeah, he's told me about all the awful shit he's been through. He's told me about his pain, in clipped bits and pieces. But desire? No. This was an outpouring I had never seen before. When he told me about his panty kink he was slightly drunk and very embarrassed. He only told me because he lost a bet.

“Fuck.” He blurted out after several moments. “I said too much.”

This was the moment I was familiar with. The regression and self-doubt. The I'm-a-worthless-piece-of-iron-testosterone-who-isn't-allowed-to-have-feelings moment that usually followed any moment of vulnerability. God, I hate John Winchester...

Dean pushed himself off the mattress.

“Where are you going?” I asked.

“Well I can't imagine you want to sit here all night with a goddamn pussy who wants to, to, to, dress up as a fucking ballerina!” I realized then that this was the first time he realized he wanted to dress up as a fucking ballerina.

“Love.” I said sternly. He growled and turned away from me, grabbing the back of his head with both hands. “First of all, you know how much I love pussy. Second of all, sit your ass down.” I pointed to the space on the bed beside me. Reluctantly he threw himself onto the mattress, elbows on his knees, face in his hands. I had discovered Dean's submissive nature not long after meeting him. I learned very quickly that giving commands, rather than arguing points, seemed to yield better results with him. How much he knew about his submissive nature? Well, I was working up to that.

I quietly slid off the bed. He snapped his head up, his big, green, scared eyes darting from me to the door.

When we first started dating, or sleeping together, or being one instead of two, or what ever this is, his lack of faith in me bothered me immensely. By now I had learned that it wasn't about me. His mother left him. His father left him, over and over. His brother left him for college. When Sam came back, it was only reluctantly and even then Sammy would piss off for a few months at a time. Cas has even been known to abandon Dean. It wasn't about me. It was about years of abuse and neglect culminating into one giant mess of a man who can't trust anyone because he doesn't believe he's worth their time or affection.

“I'm not going anywhere, love.” I nearly whispered. I pushed him back down onto the mattress when he started to get up. Kneeling before him I grasped his face firmly between my hands, forcing him to look at me. “You are the most goddamn, mother-fucking, beautiful son of a bitch I have ever had the pleasure to lay eyes.” And I kissed him fiercely.

* * *

The next few weeks were easy. We cleaned out a vamp nest in Nebraska and put down a rising werewolf epidemic out in Washington. Dean drank slightly less than usual and smiled slightly more than usual. But finding and repairing a ballerina costume, especially one to fit that big galoot, was definitely not easy. The tutu was easy, as well as the tights. But the slippers? I learned very quickly that ballet slippers are hella expensive! Eventually I just opted to find very large pink satin slippers and I sewed ribbons onto them. All together it took about 3 weeks to pull together.

That evening Dean and I, plus Sam and Cas, were on our way to Iowa to check out a weird string of disappearances. We weren't in a hurry and decided to stop for the night a little earlier than usual (per my suggestion). Before we got to the motel I silently prayed to Cas that I would have Dean to myself tonight and we could have lots of privacy. As we pulled into the parking lot he turned around in his seat and shot me a dopey grin. Lately Dean had been with me more than Cas, but Cas didn't mind. Even though we both shared very intimate relationships with Dean, they were both unique and of a different nature.

“I'm going to go … hang out in the bunker tonight.” Cas rumbled.

Dean smirked “'hang out,' ok, whatever that means. You don't 'hang out.'”

“I have an entire night to fill and I was considering using it to experiment with food. I do miss PB&J. There must be a way for an angel to enjoy food.” Cas dramatically frowned and -poof- he was gone. But not before giving me a subtle wink.

“What was that about?” Sam interjected.

“I don't know, man. Dude's always been weird.”

Dean jumped in the shower almost immediately after we got to our room. I listened to him humming Metallica as I carefully took out the surprise I made for him and laid it out on the bed. I stretched the tights out and set the tutu on top. The slippers I hid under the bed. I pulled up the desk chair and sat there waiting, not so patiently, for my pretty ballerina to get done with his shower. The water stopped and I heard the slap of wet feet on tile. A few seconds later, out emerged a tall, naked, bowlegged, lean body, vigorously toweling off his hair and still humming “Mr. Sandman.” The humming stopped abruptly as Dean took the towel away from his face and noticed the tights and the tutu resting upon our bed.

“Uh.” He sputtered after a momentary lapse. Heat crept into his cheeks and neck.

“Do you like them?” I asked tentatively. He hesitated. Those green eyes were open so wide I was afraid they'd fall out as he whipped his head back and forth from the tutu to me to the tights to the tutu to me to the tutu. “You don't have to wear them if you don't want to. I mean. I got them for you if you want them but if you don't want them I won't be crushed or anything.” That was a lie. I really wanted to see Dean Winchester in a tutu. By this time I could feel my own ears turning a delicate shade of pink.

After a moment Dean let out a flustered, nervous, almost panicked sort of laugh. “For me?!” Eyes still wide as ever.

“Yes, love.”

Dean took a hesitant step toward the bed, reached out and gently grasped the hem of his new tutu between his thumb and finger, rubbing it slowly. Almost immediately his cock gave a twitch. In seemingly no time Dean had a full-on, pulsing erection as he continued to stare at the fabric between his fingers.

“I'm going to assume you like it.” I smiled.

“hmm?” Came his vague reply as he turned to me. I shot a glance down at his engorged member, already dripping with precum. He looked down and gave a little start at the sight of his giant boner.

“We can skip the tights,” I said, grinning. Dean nodded. I stood up from my seat where I had been enjoying the view and took the tutu in my hands. His eyes followed it longingly. I let as much of the fabric graze his skin as possible as I wrapped it around him and fastened it in the back. He whimpered just the slightest bit when it brushed against the head of his cock. I smiled at this and looked up into his face. God, those eyes and those freckles and the little crow's feet and the dimples never got old.

“I have something else for you.” His eyes once again became perfect circles.

“You do?” He choked out. He sounded like his throat was dry and it must have felt it too as he cleared it just then. I bent down and reached under the bed, retrieving the “ballet” slippers I stashed there for him.

“You got me ballet slippers?” He sobbed out. Picking them up, almost reverently, he ran his hands all over their pink surface, soaking in as much of the satiny feeling as he could. He sniffled as a fat tear rolled down his cheek.

“Sit.” I told him, still smiling like an idiot. He sat on the bed, clutching his new ballet slippers, his erection standing straight up, making the pink tutu incapable of hiding anything. Kneeling in front of him, I gingerly removed the slippers from his grasp. I grabbed the back of his ankle to pull his foot up as I slid the first slipper on. I did the same with the other. Next I snugly tied the ribbons, criss-crossing them up his firm calves, ending with a neat little bow at the back.

“They're really pretty” he mumbled, running his fingers through my hair with one hand.

I looked up at his beautiful face. “You're really pretty.”

He laughed and sniffled again. “Really?”

“Really really.” I bent down and kissed the top of his foot that was exposed, moving up to kiss the places between the ribbons. I continued trailing kisses and caresses up his legs, stopping just before his thighs met. I let my tongue follow the trail of precum that was running down his cock and Dean let out a long groan. I planted my palm firmly in the middle of his chest and pushed him down onto his back. He did not resist. Nudging his legs open I wrapped my hand around his cock and balls, gripping firmly as I took his entire length into my mouth. Dean let out a sharp hiss and twisted his hands into the sheets as I began to slowly bob my head up and down on him, swirling my tongue around his head, and using my thumb to firmly rub circles around his perineum. Pulling my face off his cock with gasp, I pumped distractedly with one hand while I coated a finger of the other with my own saliva. He jumped when I touched his entrance, but relaxed as I swirled wet little circles around the tight muscle.

I stilled my hand on his cock and looked up at him. He was panting now, head thrown back, beads of sweat popping up on his forehead. “Is this ok?” I asked him, my finger resting on his asshole. He nodded and whimpered, pulling his knees up, completely exposing himself to me. I gave a little push and he gave an enormous groan as I let my finger slip inside him, until I found that sweet spot, a little bulb of pleasure. Dean arched his back and moaned, balling up more of the bed sheets into his fists. I watched him for a moment, all the muscles in his neck taught, jaw clenched, eyes squeezed shut, chest heaving as little rasps and hisses and groans escaped his mouth. His breath hitched and he cried out when I sucked one of his testicles into my mouth and swirled it around with my tongue as I continued to work my finger inside of him. I pumped my free hand up and down his cock, pulling his skin over his head on the way up, and forcing the corona of his cock to pop through the ring I made with my fingers on the way down. I pumped him harder when I felt him hold his breath a moment.

“I—I—I” He was sputtering.

“Come for me, Love.” I said as I brought my head back up to watch his face. By now I was pumping him as hard as I could, while rubbing inside of him just as vigorously. Dean let out a long grunt as come spilled out of him, dripping onto my hand, and shooting onto my hair and neck. And all over his pink tutu. I sucked the last few drops out, helping them along with a couple squeezes, and slowly retracted my finger from his hole. Dean lay on the bed, spread eagle, his whole body limp and heaving. After he began to catch his breath he looked up at me, his cheeks flushed and damp. He smiled an exhausted smile and I grinned back, raising my hand to my mouth to lick his come off myself. Before my fingers reached my lips, however, Dean snatched my wrist and pulled me to him, bringing my come-drenched fingers to his own lips, cleaning them off with his tongue. This was unexpected. He smirked, raising an eyebrow at me as if to say “bet you didn't see that coming.”

“So I take if you like your tutu and your slippers?” I asked as I curled up beside him on the bed.

Dean looked down at his tutu, “oh yeah.” His face was full of satisfaction as he ran his hand over the fabric. When his hand came back wet, however, he frowned and said “shit. I jizzed on my new tutu.”

* * *

The next morning as we were packing up and getting ready to hit the road again, Dean found his tights on the floor at the end of the bed.

“Kinda wish I had worn these,” he told me, holding them in his hands.

“So wear them.” I deadpanned, continuing to pack my own things into my backpack. He didn't say anything as I stepped into the bathroom to brush my teeth. When I came back out Dean was dressed and waiting for me at the door, with both our bags in hand, and a sheepish grin on his face.

“What?” I said, half frowning, half smiling, as I paused in the doorway. Dean grinned and lifted up his shirt and jacket. Above his blue jeans peaked the top of his pink tights.


End file.
